# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5a
_audit_block_doi                 10.5517/cc1jm18g
_database_code_depnum_ccdc_archive 'CCDC 1418475'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.5b02416 2015
_audit_update_record             
;
2015-08-13 deposited with the CCDC.
2016-04-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H17 As'
_chemical_formula_moiety         'C22 H17 As'
_chemical_formula_weight         356.30
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   12.2262(4)
_cell_length_b                   6.03311(18)
_cell_length_c                   12.5465(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 115.2163(10)
_cell_angle_gamma                90.0000
_cell_volume                     837.27(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7173
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.45
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364.00
_exptl_absorpt_coefficient_mu    2.027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.588
_exptl_absorpt_correction_T_max  0.817

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8291
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.071
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F² > 2.0 sigma(F²).
    The weighted     R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3761
_reflns_number_gt                3060
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0409
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3060
_refine_ls_number_parameters     226
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[1.0000σ(Fo²)]/(4Fo²)'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1666 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.983(8)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
As As 0.0499 2.0058
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
As1 As 0.62523(2) 0.43305(11) 0.91181(2) 0.03803(6) Uani 1 2 d . . .
C1 C 0.52292(18) 0.6532(4) 0.8012(2) 0.0362(7) Uani 1 2 d . . .
C2 C 0.52252(19) 0.8380(4) 0.8598(2) 0.0414(7) Uani 1 2 d . . .
C3 C 0.60116(19) 0.8445(4) 0.9847(2) 0.0410(7) Uani 1 2 d . . .
C4 C 0.66948(19) 0.6636(4) 1.0322(2) 0.0371(7) Uani 1 2 d . . .
C5 C 0.45012(19) 0.6105(4) 0.6757(2) 0.0401(7) Uani 1 2 d . . .
C6 C 0.46217(18) 0.4178(8) 0.6216(2) 0.0514(7) Uani 1 2 d . . .
C7 C 0.3947(2) 0.3783(4) 0.5024(3) 0.0623(11) Uani 1 2 d . . .
C8 C 0.3122(3) 0.5311(5) 0.4348(3) 0.0698(11) Uani 1 2 d . . .
C9 C 0.2969(3) 0.7241(5) 0.4857(3) 0.0713(10) Uani 1 2 d . . .
C10 C 0.3648(2) 0.7630(5) 0.6039(3) 0.0583(9) Uani 1 2 d . . .
C11 C 0.74897(18) 0.6288(4) 1.1564(2) 0.0378(7) Uani 1 2 d . . .
C12 C 0.81932(18) 0.4382(9) 1.1957(2) 0.0522(7) Uani 1 2 d . . .
C13 C 0.8933(2) 0.4020(8) 1.3138(3) 0.0630(10) Uani 1 2 d . . .
C14 C 0.8992(2) 0.5595(5) 1.3962(3) 0.0672(10) Uani 1 2 d . . .
C15 C 0.8307(2) 0.7488(5) 1.3603(3) 0.0612(9) Uani 1 2 d . . .
C16 C 0.7572(2) 0.7822(4) 1.2426(2) 0.0490(8) Uani 1 2 d . . .
C17 C 0.76600(14) 0.4304(7) 0.87566(17) 0.0387(5) Uani 1 2 d . . .
C18 C 0.7951(2) 0.6072(5) 0.8225(3) 0.0521(9) Uani 1 2 d . . .
C19 C 0.8946(3) 0.5951(6) 0.7961(3) 0.0667(11) Uani 1 2 d . . .
C20 C 0.9656(2) 0.4081(9) 0.8256(3) 0.0681(10) Uani 1 2 d . . .
C21 C 0.9379(3) 0.2361(5) 0.8792(3) 0.0667(11) Uani 1 2 d . . .
C22 C 0.8385(2) 0.2448(5) 0.9039(3) 0.0530(9) Uani 1 2 d . . .
H1 H 0.47336 0.95745 0.8216 0.0503 Uiso 1 2 calc R . .
H2 H 0.60531 0.96721 1.03109 0.0524 Uiso 1 2 calc R . .
H3 H 0.51705 0.31082 0.66685 0.0616 Uiso 1 2 calc R . .
H4 H 0.40483 0.24766 0.46825 0.0756 Uiso 1 2 calc R . .
H5 H 0.26654 0.50388 0.35498 0.0805 Uiso 1 2 calc R . .
H6 H 0.24178 0.82934 0.43893 0.0784 Uiso 1 2 calc R . .
H7 H 0.35178 0.8918 0.63764 0.0674 Uiso 1 2 calc R . .
H8 H 0.81393 0.33023 1.14075 0.0630 Uiso 1 2 calc R . .
H9 H 0.94061 0.275 1.33858 0.0728 Uiso 1 2 calc R . .
H10 H 0.9496 0.53841 1.47563 0.0774 Uiso 1 2 calc R . .
H11 H 0.83444 0.85401 1.4159 0.0724 Uiso 1 2 calc R . .
H12 H 0.71019 0.90976 1.21929 0.0588 Uiso 1 2 calc R . .
H13 H 0.74831 0.7352 0.80574 0.0640 Uiso 1 2 calc R . .
H14 H 0.91233 0.71334 0.75859 0.0858 Uiso 1 2 calc R . .
H15 H 1.03233 0.40021 0.80838 0.0842 Uiso 1 2 calc R . .
H16 H 0.98702 0.11101 0.8989 0.0810 Uiso 1 2 calc R . .
H17 H 0.81938 0.12505 0.93954 0.0635 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
As1 C1 1.943(2) yes . .
As1 C4 1.953(2) yes . .
As1 C17 1.958(2) yes . .
C1 C2 1.336(3) yes . .
C1 C5 1.465(3) yes . .
C2 C3 1.448(3) yes . .
C3 C4 1.349(3) yes . .
C4 C11 1.458(3) yes . .
C5 C6 1.385(5) yes . .
C5 C10 1.395(3) yes . .
C6 C7 1.386(4) yes . .
C7 C8 1.363(4) yes . .
C8 C9 1.378(5) yes . .
C9 C10 1.377(4) yes . .
C11 C12 1.394(5) yes . .
C11 C16 1.394(4) yes . .
C12 C13 1.385(3) yes . .
C13 C14 1.384(5) yes . .
C14 C15 1.374(4) yes . .
C15 C16 1.377(4) yes . .
C17 C18 1.383(5) yes . .
C17 C22 1.377(4) yes . .
C18 C19 1.392(5) yes . .
C19 C20 1.375(6) yes . .
C20 C21 1.355(6) yes . .
C21 C22 1.377(5) yes . .
C2 H1 0.930 no . .
C3 H2 0.930 no . .
C6 H3 0.930 no . .
C7 H4 0.930 no . .
C8 H5 0.930 no . .
C9 H6 0.930 no . .
C10 H7 0.930 no . .
C12 H8 0.930 no . .
C13 H9 0.930 no . .
C14 H10 0.930 no . .
C15 H11 0.930 no . .
C16 H12 0.930 no . .
C18 H13 0.930 no . .
C19 H14 0.930 no . .
C20 H15 0.930 no . .
C21 H16 0.930 no . .
C22 H17 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 As1 C4 86.98(10) yes . . .
C1 As1 C17 101.67(13) yes . . .
C4 As1 C17 101.76(13) yes . . .
As1 C1 C2 109.25(17) yes . . .
As1 C1 C5 123.99(16) yes . . .
C2 C1 C5 126.53(19) yes . . .
C1 C2 C3 117.46(19) yes . . .
C2 C3 C4 117.2(2) yes . . .
As1 C4 C3 108.60(16) yes . . .
As1 C4 C11 124.26(16) yes . . .
C3 C4 C11 126.5(2) yes . . .
C1 C5 C6 122.1(2) yes . . .
C1 C5 C10 121.5(2) yes . . .
C6 C5 C10 116.4(2) yes . . .
C5 C6 C7 122.3(3) yes . . .
C6 C7 C8 119.8(3) yes . . .
C7 C8 C9 119.6(3) yes . . .
C8 C9 C10 120.3(3) yes . . .
C5 C10 C9 121.6(3) yes . . .
C4 C11 C12 121.8(2) yes . . .
C4 C11 C16 121.9(2) yes . . .
C12 C11 C16 116.3(2) yes . . .
C11 C12 C13 122.1(4) yes . . .
C12 C13 C14 119.6(4) yes . . .
C13 C14 C15 119.7(3) yes . . .
C14 C15 C16 120.1(3) yes . . .
C11 C16 C15 122.2(2) yes . . .
As1 C17 C18 122.5(2) yes . . .
As1 C17 C22 118.7(3) yes . . .
C18 C17 C22 118.8(2) yes . . .
C17 C18 C19 120.3(3) yes . . .
C18 C19 C20 119.7(3) yes . . .
C19 C20 C21 119.9(3) yes . . .
C20 C21 C22 120.9(3) yes . . .
C17 C22 C21 120.4(3) yes . . .
C1 C2 H1 121.068 no . . .
C3 C2 H1 121.474 no . . .
C2 C3 H2 122.210 no . . .
C4 C3 H2 120.585 no . . .
C5 C6 H3 118.870 no . . .
C7 C6 H3 118.823 no . . .
C6 C7 H4 120.534 no . . .
C8 C7 H4 119.657 no . . .
C7 C8 H5 119.742 no . . .
C9 C8 H5 120.686 no . . .
C8 C9 H6 119.301 no . . .
C10 C9 H6 120.348 no . . .
C5 C10 H7 118.891 no . . .
C9 C10 H7 119.450 no . . .
C11 C12 H8 118.490 no . . .
C13 C12 H8 119.363 no . . .
C12 C13 H9 121.129 no . . .
C14 C13 H9 119.274 no . . .
C13 C14 H10 120.429 no . . .
C15 C14 H10 119.892 no . . .
C14 C15 H11 119.529 no . . .
C16 C15 H11 120.359 no . . .
C11 C16 H12 118.322 no . . .
C15 C16 H12 119.464 no . . .
C17 C18 H13 119.331 no . . .
C19 C18 H13 120.363 no . . .
C18 C19 H14 119.729 no . . .
C20 C19 H14 120.613 no . . .
C19 C20 H15 119.676 no . . .
C21 C20 H15 120.386 no . . .
C20 C21 H16 118.896 no . . .
C22 C21 H16 120.201 no . . .
C17 C22 H17 119.308 no . . .
C21 C22 H17 120.324 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 As1 C4 C3 6.20(17) no . . . .
C1 As1 C4 C11 177.2(2) no . . . .
C4 As1 C1 C2 -6.04(16) no . . . .
C4 As1 C1 C5 179.1(2) no . . . .
C1 As1 C17 C18 22.85(19) no . . . .
C1 As1 C17 C22 -156.89(14) no . . . .
C17 As1 C1 C2 -107.43(18) no . . . .
C17 As1 C1 C5 77.8(2) no . . . .
C4 As1 C17 C18 -66.46(16) no . . . .
C4 As1 C17 C22 113.79(17) no . . . .
C17 As1 C4 C3 107.50(18) no . . . .
C17 As1 C4 C11 -81.5(2) no . . . .
As1 C1 C2 C3 4.7(3) no . . . .
As1 C1 C5 C6 -9.9(4) no . . . .
As1 C1 C5 C10 170.25(17) no . . . .
C2 C1 C5 C6 176.2(2) no . . . .
C2 C1 C5 C10 -3.7(4) no . . . .
C5 C1 C2 C3 179.4(2) no . . . .
C1 C2 C3 C4 0.4(4) no . . . .
C2 C3 C4 As1 -5.3(3) no . . . .
C2 C3 C4 C11 -176.0(2) no . . . .
As1 C4 C11 C12 13.0(3) no . . . .
As1 C4 C11 C16 -165.74(16) no . . . .
C3 C4 C11 C12 -177.6(2) no . . . .
C3 C4 C11 C16 3.7(4) no . . . .
C1 C5 C6 C7 -179.0(2) no . . . .
C1 C5 C10 C9 179.4(2) no . . . .
C6 C5 C10 C9 -0.4(4) no . . . .
C10 C5 C6 C7 0.8(4) no . . . .
C5 C6 C7 C8 -0.8(5) no . . . .
C6 C7 C8 C9 0.3(5) no . . . .
C7 C8 C9 C10 0.1(5) no . . . .
C8 C9 C10 C5 -0.1(5) no . . . .
C4 C11 C12 C13 -178.8(2) no . . . .
C4 C11 C16 C15 179.0(2) no . . . .
C12 C11 C16 C15 0.2(4) no . . . .
C16 C11 C12 C13 0.1(4) no . . . .
C11 C12 C13 C14 -0.5(5) no . . . .
C12 C13 C14 C15 0.7(5) no . . . .
C13 C14 C15 C16 -0.4(5) no . . . .
C14 C15 C16 C11 -0.0(5) no . . . .
As1 C17 C18 C19 -178.48(15) no . . . .
As1 C17 C22 C21 179.63(15) no . . . .
C18 C17 C22 C21 -0.1(4) no . . . .
C22 C17 C18 C19 1.3(4) no . . . .
C17 C18 C19 C20 -1.5(4) no . . . .
C18 C19 C20 C21 0.5(5) no . . . .
C19 C20 C21 C22 0.6(5) no . . . .
C20 C21 C22 C17 -0.8(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
As1 C6 3.325(2) no . .
As1 C12 3.334(2) no . .
C1 C18 3.235(4) no . .
C2 C10 2.993(3) no . .
C3 C16 2.999(3) no . .
C4 C18 3.583(5) no . .
C5 C8 2.804(4) no . .
C6 C9 2.733(5) no . .
C7 C10 2.746(4) no . .
C11 C14 2.810(4) no . .
C12 C15 2.748(5) no . .
C13 C16 2.750(5) no . .
C17 C20 2.770(4) no . .
C18 C21 2.740(4) no . .
C19 C22 2.749(5) no . .
As1 C3 3.563(3) no . 2_647
C3 As1 3.563(3) no . 2_657
As1 H1 3.5983 no . .
As1 H3 2.8767 no . .
As1 H8 2.8830 no . .
As1 H13 3.0108 no . .
As1 H17 2.9163 no . .
C1 H2 3.2319 no . .
C1 H3 2.6479 no . .
C1 H7 2.6464 no . .
C1 H13 2.7765 no . .
C2 H7 2.6971 no . .
C2 H13 3.1719 no . .
C3 H12 2.6934 no . .
C3 H13 3.4859 no . .
C4 H1 3.2366 no . .
C4 H8 2.6400 no . .
C4 H12 2.6396 no . .
C4 H13 3.3944 no . .
C5 H1 2.7151 no . .
C5 H4 3.2623 no . .
C5 H6 3.2569 no . .
C5 H13 3.3840 no . .
C6 H5 3.2189 no . .
C6 H7 3.2048 no . .
C7 H6 3.2044 no . .
C8 H3 3.2098 no . .
C8 H7 3.2245 no . .
C9 H4 3.2088 no . .
C10 H1 2.7402 no . .
C10 H3 3.2065 no . .
C10 H5 3.2319 no . .
C11 H2 2.7151 no . .
C11 H9 3.2723 no . .
C11 H11 3.2620 no . .
C12 H10 3.2360 no . .
C12 H12 3.2093 no . .
C13 H11 3.2220 no . .
C14 H8 3.2292 no . .
C14 H12 3.2193 no . .
C15 H9 3.2190 no . .
C16 H2 2.7456 no . .
C16 H8 3.2101 no . .
C16 H10 3.2224 no . .
C17 H3 3.1391 no . .
C17 H8 3.1796 no . .
C17 H14 3.2421 no . .
C17 H16 3.2294 no . .
C18 H3 3.5933 no . .
C18 H15 3.2315 no . .
C18 H17 3.2149 no . .
C19 H16 3.1980 no . .
C20 H13 3.2328 no . .
C20 H17 3.2143 no . .
C21 H14 3.2055 no . .
C22 H8 3.1536 no . .
C22 H13 3.2140 no . .
C22 H15 3.2178 no . .
H1 H2 2.4293 no . .
H1 H7 2.1841 no . .
H2 H12 2.1817 no . .
H3 H4 2.3073 no . .
H4 H5 2.2848 no . .
H5 H6 2.3083 no . .
H6 H7 2.3042 no . .
H8 H9 2.3227 no . .
H8 H17 2.8378 no . .
H9 H10 2.3094 no . .
H10 H11 2.2957 no . .
H11 H12 2.3050 no . .
H13 H14 2.3237 no . .
H14 H15 2.3088 no . .
H15 H16 2.2753 no . .
H16 H17 2.3148 no . .
As1 H1 3.3423 no . 1_545
As1 H2 3.2416 no . 1_545
As1 H2 3.1970 no . 2_647
C1 H2 3.3096 no . 2_647
C1 H12 3.1178 no . 2_647
C2 H2 3.3382 no . 2_647
C3 H2 3.3417 no . 2_647
C3 H17 3.4045 no . 1_565
C4 H1 3.2697 no . 2_647
C4 H2 3.3239 no . 2_647
C5 H4 3.1335 no . 2_656
C5 H11 3.5231 no . 2_647
C5 H12 3.0407 no . 2_647
C6 H4 3.0717 no . 2_656
C6 H7 3.4879 no . 1_545
C6 H11 3.4738 no . 2_647
C6 H12 3.4663 no . 2_647
C7 H4 3.2155 no . 2_656
C7 H7 3.5394 no . 1_545
C7 H11 3.3718 no . 2_647
C8 H3 3.3324 no . 2_656
C8 H4 3.4020 no . 2_656
C8 H11 3.2746 no . 2_647
C8 H13 3.3075 no . 2_646
C8 H14 3.3794 no . 2_646
C9 H3 3.5799 no . 2_656
C9 H4 3.4655 no . 1_565
C9 H4 3.4427 no . 2_656
C9 H11 3.2836 no . 2_647
C10 H4 3.5208 no . 1_565
C10 H4 3.3073 no . 2_656
C10 H11 3.4010 no . 2_647
C10 H12 3.4691 no . 2_647
C11 H1 3.0288 no . 2_647
C11 H7 3.5990 no . 2_647
C11 H15 3.0032 no . 2_757
C11 H16 3.5804 no . 2_757
C12 H1 3.4934 no . 2_647
C12 H7 3.5431 no . 2_647
C12 H12 3.5167 no . 1_545
C12 H14 3.3660 no . 2_747
C12 H15 3.3380 no . 2_757
C12 H16 3.2399 no . 2_757
C13 H7 3.3035 no . 2_647
C13 H10 3.3402 no . 2_748
C13 H14 3.0990 no . 2_747
C14 H6 3.4950 no . 2_647
C14 H7 3.0840 no . 2_647
C14 H9 3.3231 no . 2_758
C14 H10 3.4375 no . 2_758
C14 H11 3.3400 no . 2_748
C15 H7 3.1095 no . 2_647
C15 H9 3.5026 no . 1_565
C15 H10 3.1293 no . 2_758
C15 H15 3.3368 no . 2_757
C16 H1 3.2396 no . 2_647
C16 H7 3.3589 no . 2_647
C16 H15 2.9907 no . 2_757
C17 H16 3.3209 no . 2_757
C18 H4 3.5218 no . 2_656
C18 H5 3.1342 no . 2_656
C18 H6 3.5376 no . 2_646
C18 H16 3.3734 no . 2_757
C18 H17 3.4105 no . 1_565
C19 H5 3.2211 no . 2_656
C19 H6 3.1398 no . 2_646
C19 H8 3.5964 no . 2_757
C19 H9 3.3159 no . 2_757
C19 H16 3.3743 no . 1_565
C19 H16 3.4678 no . 2_757
C20 H6 3.2403 no . 2_646
C20 H9 3.5316 no . 2_757
C20 H16 3.4750 no . 2_757
C20 H17 3.2721 no . 2_757
C21 H5 3.2541 no . 2_646
C21 H14 3.4546 no . 1_545
C21 H16 3.3954 no . 2_757
C22 H5 3.2799 no . 2_646
C22 H13 3.3206 no . 1_545
C22 H16 3.3253 no . 2_757
H1 As1 3.3423 no . 1_565
H1 C4 3.2697 no . 2_657
H1 C11 3.0288 no . 2_657
H1 C12 3.4934 no . 2_657
H1 C16 3.2396 no . 2_657
H1 H3 3.0796 no . 1_565
H1 H12 3.4300 no . 2_657
H2 As1 3.2416 no . 1_565
H2 As1 3.1970 no . 2_657
H2 C1 3.3096 no . 2_657
H2 C2 3.3382 no . 2_657
H2 C3 3.3417 no . 2_657
H2 C4 3.3239 no . 2_657
H2 H8 3.1946 no . 1_565
H2 H17 3.4114 no . 1_565
H3 C8 3.3324 no . 2_646
H3 C9 3.5799 no . 2_646
H3 H1 3.0796 no . 1_545
H3 H4 3.4800 no . 2_656
H3 H5 3.3350 no . 2_646
H3 H7 3.1586 no . 1_545
H4 C5 3.1335 no . 2_646
H4 C6 3.0717 no . 2_646
H4 C7 3.2155 no . 2_646
H4 C8 3.4020 no . 2_646
H4 C9 3.4655 no . 1_545
H4 C9 3.4427 no . 2_646
H4 C10 3.5208 no . 1_545
H4 C10 3.3073 no . 2_646
H4 C18 3.5218 no . 2_646
H4 H3 3.4800 no . 2_646
H4 H6 3.1391 no . 1_545
H4 H7 3.2743 no . 1_545
H4 H13 3.1376 no . 2_646
H5 C18 3.1342 no . 2_646
H5 C19 3.2211 no . 2_646
H5 C21 3.2541 no . 2_656
H5 C22 3.2799 no . 2_656
H5 H3 3.3350 no . 2_656
H5 H13 2.5327 no . 2_646
H5 H14 2.6889 no . 2_646
H5 H16 3.4294 no . 2_656
H5 H17 3.4619 no . 2_656
H6 C14 3.4950 no . 2_657
H6 C18 3.5376 no . 2_656
H6 C19 3.1398 no . 2_656
H6 C20 3.2403 no . 2_656
H6 H4 3.1391 no . 1_565
H6 H10 3.2175 no . 2_657
H6 H14 3.3287 no . 2_656
H6 H15 3.4902 no . 2_656
H7 C6 3.4879 no . 1_565
H7 C7 3.5394 no . 1_565
H7 C11 3.5990 no . 2_657
H7 C12 3.5431 no . 2_657
H7 C13 3.3035 no . 2_657
H7 C14 3.0840 no . 2_657
H7 C15 3.1095 no . 2_657
H7 C16 3.3589 no . 2_657
H7 H3 3.1586 no . 1_565
H7 H4 3.2743 no . 1_565
H7 H10 3.4521 no . 2_657
H7 H11 3.4796 no . 2_657
H8 C19 3.5964 no . 2_747
H8 H2 3.1946 no . 1_545
H8 H12 3.1749 no . 1_545
H8 H14 3.1132 no . 2_747
H8 H15 3.1063 no . 2_747
H8 H16 3.1735 no . 2_757
H9 C14 3.3231 no . 2_748
H9 C15 3.5026 no . 1_545
H9 C19 3.3159 no . 2_747
H9 C20 3.5316 no . 2_747
H9 H10 2.5704 no . 2_748
H9 H11 3.1859 no . 1_545
H9 H11 3.1720 no . 2_748
H9 H12 3.3822 no . 1_545
H9 H14 2.5933 no . 2_747
H9 H15 3.0235 no . 2_747
H10 C13 3.3402 no . 2_758
H10 C14 3.4375 no . 2_748
H10 C15 3.1293 no . 2_748
H10 H6 3.2175 no . 2_647
H10 H7 3.4521 no . 2_647
H10 H9 2.5704 no . 2_758
H10 H10 3.2172 no . 2_748
H10 H10 3.2172 no . 2_758
H10 H11 2.6457 no . 2_748
H11 C5 3.5231 no . 2_657
H11 C6 3.4738 no . 2_657
H11 C7 3.3718 no . 2_657
H11 C8 3.2746 no . 2_657
H11 C9 3.2836 no . 2_657
H11 C10 3.4010 no . 2_657
H11 C14 3.3400 no . 2_758
H11 H7 3.4796 no . 2_647
H11 H9 3.1859 no . 1_565
H11 H9 3.1720 no . 2_758
H11 H10 2.6457 no . 2_758
H12 C1 3.1178 no . 2_657
H12 C5 3.0407 no . 2_657
H12 C6 3.4663 no . 2_657
H12 C10 3.4691 no . 2_657
H12 C12 3.5167 no . 1_565
H12 H1 3.4300 no . 2_647
H12 H8 3.1749 no . 1_565
H12 H9 3.3822 no . 1_565
H12 H15 3.3113 no . 2_757
H13 C8 3.3075 no . 2_656
H13 C22 3.3206 no . 1_565
H13 H4 3.1376 no . 2_656
H13 H5 2.5327 no . 2_656
H13 H16 3.4811 no . 1_565
H13 H17 2.8040 no . 1_565
H14 C8 3.3794 no . 2_656
H14 C12 3.3660 no . 2_757
H14 C13 3.0990 no . 2_757
H14 C21 3.4546 no . 1_565
H14 H5 2.6889 no . 2_656
H14 H6 3.3287 no . 2_646
H14 H8 3.1132 no . 2_757
H14 H9 2.5933 no . 2_757
H14 H16 2.8843 no . 1_565
H15 C11 3.0032 no . 2_747
H15 C12 3.3380 no . 2_747
H15 C15 3.3368 no . 2_747
H15 C16 2.9907 no . 2_747
H15 H6 3.4902 no . 2_646
H15 H8 3.1063 no . 2_757
H15 H9 3.0235 no . 2_757
H15 H12 3.3113 no . 2_747
H15 H17 3.2006 no . 2_757
H16 C11 3.5804 no . 2_747
H16 C12 3.2399 no . 2_747
H16 C17 3.3209 no . 2_747
H16 C18 3.3734 no . 2_747
H16 C19 3.3743 no . 1_545
H16 C19 3.4678 no . 2_747
H16 C20 3.4750 no . 2_747
H16 C21 3.3954 no . 2_747
H16 C22 3.3253 no . 2_747
H16 H5 3.4294 no . 2_646
H16 H8 3.1735 no . 2_747
H16 H13 3.4811 no . 1_545
H16 H14 2.8843 no . 1_545
H17 C3 3.4045 no . 1_545
H17 C18 3.4105 no . 1_545
H17 C20 3.2721 no . 2_747
H17 H2 3.4114 no . 1_545
H17 H5 3.4619 no . 2_646
H17 H13 2.8040 no . 1_545
H17 H15 3.2006 no . 2_747

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5b
_audit_block_doi                 10.5517/cc1jm1bj
_database_code_depnum_ccdc_archive 'CCDC 1418477'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.5b02416 2015
_audit_update_record             
;
2015-08-13 deposited with the CCDC.
2016-04-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H21 As O2'
_chemical_formula_moiety         'C24 H21 As O2'
_chemical_formula_weight         416.35
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
_space_group_IT_number           62
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2+Z
3 +X,1/2-Y,+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,1/2-Z
7 -X,1/2+Y,-Z
8 1/2+X,+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.88163(18)
_cell_length_b                   16.2823(4)
_cell_length_c                   15.3253(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1966.72(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14074
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.44
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856.00
_exptl_absorpt_coefficient_mu    1.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.530
_exptl_absorpt_correction_T_max  0.705

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            18387
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.164
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F² > 2.0 sigma(F²).
    The weighted     R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2322
_reflns_number_gt                1980
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1980
_refine_ls_number_parameters     151
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[0.0015Fo² + 1.0000σ(Fo²)]/(4Fo²)'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.273
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
As As 0.0499 2.0058
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
As1 As 0.47921(3) 0.25 0.08604(2) 0.04016(10) Uani 1 4 d . . .
O1 O 0.6658(2) 0.42365(9) 0.09569(9) 0.0524(4) Uani 1 8 d . . .
C1 C 0.4005(2) 0.33231(11) 0.17012(12) 0.0399(5) Uani 1 8 d . . .
C2 C 0.3487(3) 0.29451(11) 0.24335(11) 0.0436(5) Uani 1 8 d . . .
C3 C 0.3922(2) 0.42179(11) 0.15612(12) 0.0411(5) Uani 1 8 d . . .
C4 C 0.5247(2) 0.46730(13) 0.11874(14) 0.0442(5) Uani 1 8 d . . .
C5 C 0.5108(3) 0.55200(15) 0.1098(2) 0.0577(7) Uani 1 8 d . . .
C6 C 0.3653(4) 0.59114(14) 0.13715(18) 0.0693(8) Uani 1 8 d . . .
C7 C 0.2339(3) 0.54855(14) 0.17463(17) 0.0653(7) Uani 1 8 d . . .
C8 C 0.2474(3) 0.46398(12) 0.18294(14) 0.0518(6) Uani 1 8 d . . .
C9 C 0.8106(3) 0.46859(16) 0.06729(18) 0.0687(8) Uani 1 8 d . . .
C10 C 0.2766(4) 0.25 0.01093(17) 0.0424(7) Uani 1 4 d . . .
C11 C 0.2988(5) 0.250000(10) -0.07851(18) 0.0536(9) Uani 1 4 d . . .
C12 C 0.1581(6) 0.250000(10) -0.1342(2) 0.0746(12) Uani 1 4 d . . .
C13 C -0.0002(5) 0.250000(10) -0.1009(3) 0.0764(14) Uani 1 4 d . . .
C14 C -0.0263(5) 0.250000(10) -0.0128(4) 0.0838(16) Uani 1 4 d . . .
C15 C 0.1122(4) 0.250000(10) 0.0439(3) 0.0698(11) Uani 1 4 d . . .
H1 H 0.31409 0.32445 0.29187 0.0522 Uiso 1 8 calc R . .
H2 H 0.59875 0.58166 0.08441 0.0692 Uiso 1 8 calc R . .
H3 H 0.35645 0.64775 0.13044 0.0831 Uiso 1 8 calc R . .
H4 H 0.13865 0.57618 0.19519 0.0786 Uiso 1 8 calc R . .
H5 H 0.15709 0.4344 0.20613 0.0617 Uiso 1 8 calc R . .
H6 H 0.78298 0.49912 0.01563 0.0824 Uiso 1 8 calc R . .
H7 H 0.84481 0.50582 0.11257 0.0826 Uiso 1 8 calc R . .
H8 H 0.90189 0.43135 0.0548 0.0827 Uiso 1 8 calc R . .
H9 H 0.4079 0.25 -0.10161 0.0643 Uiso 1 4 calc R . .
H10 H 0.17376 0.25 -0.19434 0.0897 Uiso 1 4 calc R . .
H11 H -0.09365 0.25 -0.13791 0.0914 Uiso 1 4 calc R . .
H12 H -0.13621 0.25 0.0093 0.1006 Uiso 1 4 calc R . .
H13 H 0.09445 0.25 0.10386 0.0839 Uiso 1 4 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
As1 C1 1.9599(18) yes . .
As1 C1 1.9599(18) yes . 3_555
As1 C10 1.969(3) yes . .
O1 C4 1.366(2) yes . .
O1 C9 1.424(3) yes . .
C1 C2 1.344(3) yes . .
C1 C3 1.474(3) yes . .
C2 C2 1.449(3) yes . 3_555
C3 C4 1.402(3) yes . .
C3 C8 1.394(3) yes . .
C4 C5 1.390(3) yes . .
C5 C6 1.378(4) yes . .
C6 C7 1.372(4) yes . .
C7 C8 1.387(3) yes . .
C10 C11 1.382(4) yes . .
C10 C15 1.390(4) yes . .
C11 C12 1.399(5) yes . .
C12 C13 1.348(6) yes . .
C13 C14 1.365(8) yes . .
C14 C15 1.395(6) yes . .
C2 H1 0.930 no . .
C5 H2 0.930 no . .
C6 H3 0.930 no . .
C7 H4 0.930 no . .
C8 H5 0.930 no . .
C9 H6 0.960 no . .
C9 H7 0.960 no . .
C9 H8 0.960 no . .
C11 H9 0.930 no . .
C12 H10 0.930 no . .
C13 H11 0.930 no . .
C14 H12 0.930 no . .
C15 H13 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 As1 C1 86.29(8) yes . . 3_555
C1 As1 C10 97.34(8) yes . . .
C1 As1 C10 97.34(8) yes 3_555 . .
C4 O1 C9 117.66(17) yes . . .
As1 C1 C2 109.40(13) yes . . .
As1 C1 C3 126.45(13) yes . . .
C2 C1 C3 124.11(17) yes . . .
C1 C2 C2 117.26(16) yes . . 3_555
C1 C3 C4 123.28(17) yes . . .
C1 C3 C8 118.71(17) yes . . .
C4 C3 C8 118.00(17) yes . . .
O1 C4 C3 115.89(18) yes . . .
O1 C4 C5 123.67(19) yes . . .
C3 C4 C5 120.39(19) yes . . .
C4 C5 C6 119.6(2) yes . . .
C5 C6 C7 121.5(2) yes . . .
C6 C7 C8 118.8(2) yes . . .
C3 C8 C7 121.7(2) yes . . .
As1 C10 C11 118.5(2) yes . . .
As1 C10 C15 122.9(2) yes . . .
C11 C10 C15 118.6(3) yes . . .
C10 C11 C12 120.3(3) yes . . .
C11 C12 C13 120.1(4) yes . . .
C12 C13 C14 120.9(4) yes . . .
C13 C14 C15 119.8(4) yes . . .
C10 C15 C14 120.2(4) yes . . .
C1 C2 H1 121.124 no . . .
C2 C2 H1 121.613 no 3_555 . .
C4 C5 H2 119.859 no . . .
C6 C5 H2 120.500 no . . .
C5 C6 H3 119.149 no . . .
C7 C6 H3 119.384 no . . .
C6 C7 H4 120.421 no . . .
C8 C7 H4 120.746 no . . .
C3 C8 H5 118.957 no . . .
C7 C8 H5 119.361 no . . .
O1 C9 H6 109.641 no . . .
O1 C9 H7 109.173 no . . .
O1 C9 H8 109.690 no . . .
H6 C9 H7 109.445 no . . .
H6 C9 H8 109.438 no . . .
H7 C9 H8 109.440 no . . .
C10 C11 H9 119.648 no . . .
C12 C11 H9 120.046 no . . .
C11 C12 H10 119.939 no . . .
C13 C12 H10 119.919 no . . .
C12 C13 H11 120.080 no . . .
C14 C13 H11 118.979 no . . .
C13 C14 H12 120.011 no . . .
C15 C14 H12 120.158 no . . .
C10 C15 H13 119.952 no . . .
C14 C15 H13 119.833 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 As1 C1 C2 -5.37(12) no . . 3_555 3_555
C1 As1 C1 C3 172.64(15) no . . 3_555 3_555
C1 As1 C1 C2 5.37(12) no 3_555 . . .
C1 As1 C1 C3 -172.64(15) no 3_555 . . .
C1 As1 C10 C11 136.41(5) no . . . .
C1 As1 C10 C15 -43.59(5) no . . . .
C10 As1 C1 C2 102.30(12) no . . . .
C10 As1 C1 C3 -75.71(14) no . . . .
C1 As1 C10 C11 -136.41(5) no 3_555 . . .
C1 As1 C10 C15 43.59(5) no 3_555 . . .
C10 As1 C1 C2 -102.30(12) no . . 3_555 3_555
C10 As1 C1 C3 75.71(14) no . . 3_555 3_555
C9 O1 C4 C3 -172.65(17) no . . . .
C9 O1 C4 C5 5.0(3) no . . . .
As1 C1 C2 C2 -4.4(2) no . . . 3_555
As1 C1 C3 C4 -45.8(2) no . . . .
As1 C1 C3 C8 135.64(14) no . . . .
C2 C1 C3 C4 136.47(19) no . . . .
C2 C1 C3 C8 -42.1(3) no . . . .
C3 C1 C2 C2 173.66(15) no . . . 3_555
C1 C2 C2 C1 0.0(3) no . . 3_555 3_555
C1 C3 C4 O1 -0.3(3) no . . . .
C1 C3 C4 C5 -178.00(16) no . . . .
C1 C3 C8 C7 177.62(16) no . . . .
C4 C3 C8 C7 -1.0(3) no . . . .
C8 C3 C4 O1 178.26(16) no . . . .
C8 C3 C4 C5 0.6(3) no . . . .
O1 C4 C5 C6 -178.15(19) no . . . .
C3 C4 C5 C6 -0.6(4) no . . . .
C4 C5 C6 C7 1.2(4) no . . . .
C5 C6 C7 C8 -1.6(4) no . . . .
C6 C7 C8 C3 1.5(4) no . . . .
As1 C10 C11 C12 180.0 no . . . .
As1 C10 C15 C14 180.0 no . . . .
C11 C10 C15 C14 0.000(17) no . . . .
C15 C10 C11 C12 0.000(17) no . . . .
C10 C11 C12 C13 0.00(2) no . . . .
C11 C12 C13 C14 0.00(2) no . . . .
C12 C13 C14 C15 0.00(2) no . . . .
C13 C14 C15 C10 0.00(2) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
As1 O1 3.1905(15) no . .
As1 O1 3.1905(15) no . 3_555
As1 C2 2.7195(18) no . 3_555
As1 C3 3.0736(18) no . 3_555
As1 C4 3.591(2) no . .
As1 C4 3.591(2) no . 3_555
O1 C1 2.808(2) no . .
C1 C15 3.272(4) no . .
C2 C8 3.018(3) no . .
C3 C6 2.781(3) no . .
C4 C7 2.782(3) no . .
C5 C8 2.761(3) no . .
C5 C9 2.802(3) no . .
C10 C13 2.774(5) no . .
C11 C14 2.753(5) no . .
C12 C15 2.753(5) no . .
O1 C2 3.547(2) no . 8_555
O1 C5 3.466(3) no . 5_665
O1 C6 3.585(3) no . 5_665
O1 C8 3.515(3) no . 8_555
C2 O1 3.547(2) no . 8_455
C4 C5 3.528(4) no . 5_665
C4 C8 3.510(3) no . 8_555
C5 O1 3.466(3) no . 5_665
C5 C4 3.528(4) no . 5_665
C5 C11 3.588(3) no . 5_665
C6 O1 3.585(3) no . 5_665
C6 C9 3.562(4) no . 5_665
C8 O1 3.515(3) no . 8_455
C8 C4 3.510(3) no . 8_455
C9 C6 3.562(4) no . 5_665
C11 C5 3.588(3) no . 5_665
C11 C5 3.588(3) no . 7_645
As1 H9 2.9302 no . .
As1 H13 3.0448 no . .
O1 H2 2.6322 no . .
C1 H1 3.2343 no . 3_555
C1 H5 2.5979 no . .
C1 H13 2.9406 no . .
C2 H5 2.7918 no . .
C2 H13 3.0184 no . .
C3 H1 2.6869 no . .
C3 H2 3.2608 no . .
C3 H4 3.2669 no . .
C4 H3 3.2285 no . .
C4 H5 3.2364 no . .
C4 H6 2.6287 no . .
C4 H7 2.6016 no . .
C4 H8 3.1846 no . .
C5 H4 3.2360 no . .
C5 H6 2.7250 no . .
C5 H7 2.7378 no . .
C6 H5 3.2129 no . .
C7 H2 3.2362 no . .
C8 H1 2.8678 no . .
C8 H3 3.2155 no . .
C9 H2 2.4995 no . .
C10 H10 3.2485 no . .
C10 H12 3.2536 no . .
C11 H11 3.2242 no . .
C11 H13 3.2257 no . .
C12 H12 3.1963 no . .
C13 H9 3.2167 no . .
C13 H13 3.2248 no . .
C14 H10 3.1981 no . .
C15 H9 3.2252 no . .
C15 H11 3.2239 no . .
H1 H1 2.4244 no . 3_555
H1 H5 2.5422 no . .
H1 H13 3.5733 no . .
H2 H3 2.3027 no . .
H2 H6 2.2418 no . .
H2 H7 2.3393 no . .
H2 H8 3.4502 no . .
H3 H4 2.2999 no . .
H4 H5 2.3191 no . .
H5 H13 3.4227 no . .
H9 H10 2.3292 no . .
H10 H11 2.2782 no . .
H11 H12 2.2808 no . .
H12 H13 2.3249 no . .
As1 H1 3.4550 no . 6_555
As1 H1 3.4550 no . 8_555
As1 H12 3.2513 no . 1_655
O1 H1 2.6352 no . 8_555
O1 H2 3.4603 no . 5_665
O1 H5 3.0430 no . 8_555
O1 H12 3.4903 no . 1_655
C1 H1 3.3136 no . 8_555
C1 H5 3.2325 no . 8_555
C2 H5 3.4199 no . 8_555
C2 H13 3.1241 no . 6_555
C3 H5 2.9759 no . 8_555
C3 H6 3.2394 no . 5_665
C4 H1 3.5341 no . 8_555
C4 H2 3.3578 no . 5_665
C4 H4 3.4758 no . 8_555
C4 H5 2.9291 no . 8_555
C4 H6 3.2279 no . 5_665
C5 H4 3.1780 no . 8_555
C5 H5 3.5988 no . 8_555
C5 H6 3.1228 no . 5_665
C5 H9 3.2893 no . 5_665
C6 H4 3.3621 no . 8_555
C6 H6 3.0012 no . 5_665
C6 H9 3.1911 no . 5_665
C6 H11 3.3576 no . 5_565
C7 H6 3.0203 no . 5_665
C7 H7 3.2851 no . 1_455
C7 H7 3.4474 no . 8_455
C7 H11 3.5067 no . 5_565
C8 H6 3.1111 no . 5_665
C8 H7 3.4199 no . 1_455
C8 H7 3.2977 no . 8_455
C8 H8 3.3992 no . 1_455
C9 H1 3.1887 no . 8_555
C9 H5 3.5062 no . 1_655
C9 H6 3.4857 no . 5_765
C9 H8 3.3599 no . 5_765
C10 H2 3.2578 no . 5_665
C10 H2 3.2578 no . 7_645
C11 H2 2.8589 no . 5_665
C11 H2 2.8589 no . 7_645
C11 H3 3.2847 no . 5_665
C11 H3 3.2847 no . 7_645
C12 H2 3.4306 no . 5_665
C12 H2 3.4306 no . 7_645
C13 H3 3.2955 no . 5_565
C13 H3 3.2955 no . 7_545
C13 H4 3.3602 no . 5_565
C13 H4 3.3602 no . 7_545
C14 H3 3.5768 no . 5_565
C14 H3 3.5768 no . 7_545
C14 H8 3.1800 no . 1_455
C14 H8 3.1800 no . 3_455
C15 H8 3.3905 no . 1_455
C15 H8 3.3905 no . 3_455
H1 As1 3.4550 no . 6_455
H1 O1 2.6352 no . 8_455
H1 C1 3.3136 no . 8_455
H1 C4 3.5341 no . 8_455
H1 C9 3.1887 no . 8_455
H1 H5 3.2426 no . 8_555
H1 H7 3.3052 no . 8_455
H1 H8 3.0050 no . 8_455
H1 H12 3.3027 no . 6_555
H1 H13 2.9842 no . 6_555
H2 O1 3.4603 no . 5_665
H2 C4 3.3578 no . 5_665
H2 C10 3.2578 no . 5_665
H2 C11 2.8589 no . 5_665
H2 C12 3.4306 no . 5_665
H2 H4 3.3935 no . 8_555
H2 H9 2.7541 no . 5_665
H3 C11 3.2847 no . 5_665
H3 C13 3.2955 no . 5_565
H3 C14 3.5768 no . 5_565
H3 H3 3.3297 no . 3_565
H3 H6 3.4551 no . 5_665
H3 H9 2.5331 no . 5_665
H3 H10 3.1685 no . 2_555
H3 H11 2.6599 no . 5_565
H3 H12 3.2204 no . 5_565
H4 C4 3.4758 no . 8_455
H4 C5 3.1780 no . 8_455
H4 C6 3.3621 no . 8_455
H4 C13 3.3602 no . 5_565
H4 H2 3.3935 no . 8_455
H4 H6 3.5105 no . 5_665
H4 H7 2.8774 no . 1_455
H4 H7 3.5542 no . 8_455
H4 H11 2.9844 no . 5_565
H5 O1 3.0430 no . 8_455
H5 C1 3.2325 no . 8_455
H5 C2 3.4199 no . 8_455
H5 C3 2.9759 no . 8_455
H5 C4 2.9291 no . 8_455
H5 C5 3.5988 no . 8_455
H5 C9 3.5062 no . 1_455
H5 H1 3.2426 no . 8_455
H5 H6 3.5979 no . 5_665
H5 H7 3.0767 no . 1_455
H5 H7 3.3558 no . 8_455
H5 H8 3.0703 no . 1_455
H6 C3 3.2394 no . 5_665
H6 C4 3.2279 no . 5_665
H6 C5 3.1228 no . 5_665
H6 C6 3.0012 no . 5_665
H6 C7 3.0203 no . 5_665
H6 C8 3.1111 no . 5_665
H6 C9 3.4857 no . 5_765
H6 H3 3.4551 no . 5_665
H6 H4 3.5105 no . 5_665
H6 H5 3.5979 no . 5_665
H6 H6 3.4544 no . 5_765
H6 H7 3.5317 no . 5_765
H6 H8 2.9352 no . 5_765
H7 C7 3.2851 no . 1_655
H7 C7 3.4474 no . 8_555
H7 C8 3.4199 no . 1_655
H7 C8 3.2977 no . 8_555
H7 H1 3.3052 no . 8_555
H7 H4 2.8774 no . 1_655
H7 H4 3.5542 no . 8_555
H7 H5 3.0767 no . 1_655
H7 H5 3.3558 no . 8_555
H7 H6 3.5317 no . 5_765
H7 H8 3.4076 no . 5_765
H8 C8 3.3992 no . 1_655
H8 C9 3.3599 no . 5_765
H8 C14 3.1800 no . 1_655
H8 C15 3.3905 no . 1_655
H8 H1 3.0050 no . 8_555
H8 H5 3.0703 no . 1_655
H8 H6 2.9352 no . 5_765
H8 H7 3.4076 no . 5_765
H8 H8 3.1954 no . 5_765
H8 H12 3.0488 no . 1_655
H8 H13 3.4041 no . 1_655
H9 C5 3.2893 no . 5_665
H9 C5 3.2893 no . 7_645
H9 C6 3.1911 no . 5_665
H9 C6 3.1911 no . 7_645
H9 H2 2.7541 no . 5_665
H9 H2 2.7541 no . 7_645
H9 H3 2.5331 no . 5_665
H9 H3 2.5331 no . 7_645
H10 H3 3.1685 no . 2_544
H10 H3 3.1685 no . 4_564
H10 H11 3.1575 no . 6_554
H11 C6 3.3576 no . 5_565
H11 C6 3.3576 no . 7_545
H11 C7 3.5067 no . 5_565
H11 C7 3.5067 no . 7_545
H11 H3 2.6599 no . 5_565
H11 H3 2.6599 no . 7_545
H11 H4 2.9844 no . 5_565
H11 H4 2.9844 no . 7_545
H11 H10 3.1575 no . 6_454
H12 As1 3.2513 no . 1_455
H12 O1 3.4903 no . 1_455
H12 O1 3.4903 no . 3_455
H12 H1 3.3027 no . 6_455
H12 H1 3.3027 no . 8_455
H12 H3 3.2204 no . 5_565
H12 H3 3.2204 no . 7_545
H12 H8 3.0488 no . 1_455
H12 H8 3.0488 no . 3_455
H13 C2 3.1241 no . 6_455
H13 C2 3.1241 no . 8_455
H13 H1 2.9842 no . 6_455
H13 H1 2.9842 no . 8_455
H13 H8 3.4041 no . 1_455
H13 H8 3.4041 no . 3_455

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6a
_audit_block_doi                 10.5517/cc1jm1ck
_database_code_depnum_ccdc_archive 'CCDC 1418478'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.5b02416 2015
_audit_update_record             
;
2015-08-13 deposited with the CCDC.
2016-04-15 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C22 H17 P'
_chemical_formula_moiety         'C22 H17 P'
_chemical_formula_weight         312.35
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_symmetry_equiv_pos_site_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   12.1722(5)
_cell_length_b                   5.9237(2)
_cell_length_c                   12.6791(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 115.8923(15)
_cell_angle_gamma                90.0000
_cell_volume                     822.44(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6043
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.45
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328.00
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.984

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8042
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.091
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max ?
_diffrn_reflns_Laue_measured_fraction_full ?
_diffrn_reflns_point_group_measured_fraction_max ?
_diffrn_reflns_point_group_measured_fraction_full ?
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using reflections with F² > 2.0 sigma(F²).
    The weighted     R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             3672
_reflns_number_gt                2380
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          ?
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0618
_refine_ls_wR_factor_gt          ?
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2380
_refine_ls_number_parameters     226
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[0.0003Fo² + 1.0000σ(Fo²)]/(4Fo²)'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.186
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1606 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.98(8)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
P P 0.1023 0.0942
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.12655(5) 0.32260(11) 0.41166(5) 0.03881(15) Uani 1 2 d . . .
C1 C 0.16930(19) 0.1108(3) 0.52744(19) 0.0380(6) Uani 1 2 d . . .
C2 C 0.09728(19) -0.0717(3) 0.4825(2) 0.0424(7) Uani 1 2 d . . .
C3 C 0.01815(19) -0.0650(3) 0.3597(2) 0.0429(7) Uani 1 2 d . . .
C4 C 0.02502(18) 0.1247(3) 0.30355(19) 0.0392(6) Uani 1 2 d . . .
C5 C 0.25020(18) 0.1512(4) 0.65103(19) 0.0391(6) Uani 1 2 d . . .
C6 C 0.31987(19) 0.3461(4) 0.68978(19) 0.0515(7) Uani 1 2 d . . .
C7 C 0.3939(2) 0.3832(4) 0.8066(2) 0.0624(9) Uani 1 2 d . . .
C8 C 0.4006(3) 0.2287(5) 0.8898(2) 0.0686(9) Uani 1 2 d . . .
C9 C 0.3327(2) 0.0341(4) 0.8547(2) 0.0613(8) Uani 1 2 d . . .
C10 C 0.2591(2) -0.0043(4) 0.7373(2) 0.0512(7) Uani 1 2 d . . .
C11 C -0.04752(19) 0.1759(4) 0.1788(2) 0.0428(7) Uani 1 2 d . . .
C12 C -0.0327(2) 0.3756(4) 0.1293(2) 0.0515(8) Uani 1 2 d . . .
C13 C -0.1010(2) 0.4206(4) 0.0110(2) 0.0621(9) Uani 1 2 d . . .
C14 C -0.1860(3) 0.2687(4) -0.0595(3) 0.0695(10) Uani 1 2 d . . .
C15 C -0.2024(3) 0.0703(4) -0.0123(2) 0.0715(9) Uani 1 2 d . . .
C16 C -0.1348(2) 0.0236(4) 0.1048(2) 0.0587(8) Uani 1 2 d . . .
C17 C 0.25887(16) 0.3473(4) 0.37834(16) 0.0370(5) Uani 1 2 d . . .
C18 C 0.2921(2) 0.1758(4) 0.3241(2) 0.0513(7) Uani 1 2 d . . .
C19 C 0.3907(2) 0.2008(4) 0.2983(2) 0.0622(9) Uani 1 2 d . . .
C20 C 0.4577(2) 0.3970(4) 0.3278(2) 0.0623(8) Uani 1 2 d . . .
C21 C 0.4266(2) 0.5682(4) 0.3831(2) 0.0611(8) Uani 1 2 d . . .
C22 C 0.3269(2) 0.5438(4) 0.4074(2) 0.0510(7) Uani 1 2 d . . .
H1 H 0.0988 -0.19476 0.52862 0.0540 Uiso 1 2 calc R . .
H2 H -0.03439 -0.18308 0.32098 0.0520 Uiso 1 2 calc R . .
H3 H 0.31617 0.45458 0.63531 0.0625 Uiso 1 2 calc R . .
H4 H 0.43993 0.5148 0.83052 0.0729 Uiso 1 2 calc R . .
H5 H 0.45039 0.25391 0.96888 0.0790 Uiso 1 2 calc R . .
H6 H 0.33683 -0.07205 0.91029 0.0726 Uiso 1 2 calc R . .
H7 H 0.21426 -0.13745 0.71529 0.0609 Uiso 1 2 calc R . .
H8 H 0.02306 0.48195 0.17693 0.0609 Uiso 1 2 calc R . .
H9 H -0.08742 0.5539 -0.02027 0.0750 Uiso 1 2 calc R . .
H10 H -0.23228 0.30044 -0.1386 0.0795 Uiso 1 2 calc R . .
H11 H -0.26014 -0.0334 -0.05984 0.0777 Uiso 1 2 calc R . .
H12 H -0.14594 -0.11242 0.13552 0.0672 Uiso 1 2 calc R . .
H13 H 0.24651 0.0433 0.30329 0.0634 Uiso 1 2 calc R . .
H14 H 0.41307 0.08317 0.26305 0.0804 Uiso 1 2 calc R . .
H15 H 0.52231 0.41522 0.30815 0.0779 Uiso 1 2 calc R . .
H16 H 0.47398 0.69824 0.4066 0.0729 Uiso 1 2 calc R . .
H17 H 0.30373 0.66129 0.442 0.0629 Uiso 1 2 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
P1 C1 1.825(2) yes . .
P1 C4 1.817(2) yes . .
P1 C17 1.841(2) yes . .
C1 C2 1.351(3) yes . .
C1 C5 1.461(3) yes . .
C2 C3 1.429(3) yes . .
C3 C4 1.352(3) yes . .
C4 C11 1.468(3) yes . .
C5 C6 1.389(3) yes . .
C5 C10 1.398(4) yes . .
C6 C7 1.375(3) yes . .
C7 C8 1.371(4) yes . .
C8 C9 1.374(4) yes . .
C9 C10 1.380(3) yes . .
C11 C12 1.387(3) yes . .
C11 C16 1.397(3) yes . .
C12 C13 1.386(3) yes . .
C13 C14 1.369(3) yes . .
C14 C15 1.372(4) yes . .
C15 C16 1.375(3) yes . .
C17 C18 1.382(3) yes . .
C17 C22 1.382(3) yes . .
C18 C19 1.384(4) yes . .
C19 C20 1.374(4) yes . .
C20 C21 1.376(4) yes . .
C21 C22 1.383(4) yes . .
C2 H1 0.930 no . .
C3 H2 0.930 no . .
C6 H3 0.930 no . .
C7 H4 0.930 no . .
C8 H5 0.930 no . .
C9 H6 0.930 no . .
C10 H7 0.930 no . .
C12 H8 0.930 no . .
C13 H9 0.930 no . .
C14 H10 0.930 no . .
C15 H11 0.930 no . .
C16 H12 0.930 no . .
C18 H13 0.930 no . .
C19 H14 0.930 no . .
C20 H15 0.930 no . .
C21 H16 0.930 no . .
C22 H17 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 P1 C4 91.41(9) yes . . .
C1 P1 C17 105.57(10) yes . . .
C4 P1 C17 104.66(11) yes . . .
P1 C1 C2 107.81(15) yes . . .
P1 C1 C5 124.90(14) yes . . .
C2 C1 C5 126.3(2) yes . . .
C1 C2 C3 116.2(2) yes . . .
C2 C3 C4 115.40(17) yes . . .
P1 C4 C3 108.49(15) yes . . .
P1 C4 C11 124.81(16) yes . . .
C3 C4 C11 126.34(18) yes . . .
C1 C5 C6 122.5(2) yes . . .
C1 C5 C10 121.16(18) yes . . .
C6 C5 C10 116.37(19) yes . . .
C5 C6 C7 121.7(2) yes . . .
C6 C7 C8 120.8(2) yes . . .
C7 C8 C9 119.0(2) yes . . .
C8 C9 C10 120.2(3) yes . . .
C5 C10 C9 121.8(2) yes . . .
C4 C11 C12 121.87(18) yes . . .
C4 C11 C16 120.9(2) yes . . .
C12 C11 C16 117.3(2) yes . . .
C11 C12 C13 121.2(2) yes . . .
C12 C13 C14 120.3(3) yes . . .
C13 C14 C15 119.4(2) yes . . .
C14 C15 C16 120.7(2) yes . . .
C11 C16 C15 121.0(2) yes . . .
P1 C17 C18 122.07(17) yes . . .
P1 C17 C22 119.24(19) yes . . .
C18 C17 C22 118.7(2) yes . . .
C17 C18 C19 120.8(2) yes . . .
C18 C19 C20 119.9(3) yes . . .
C19 C20 C21 120.0(3) yes . . .
C20 C21 C22 119.9(2) yes . . .
C17 C22 C21 120.7(2) yes . . .
C1 C2 H1 122.069 no . . .
C3 C2 H1 121.707 no . . .
C2 C3 H2 122.348 no . . .
C4 C3 H2 122.248 no . . .
C5 C6 H3 119.186 no . . .
C7 C6 H3 119.086 no . . .
C6 C7 H4 120.213 no . . .
C8 C7 H4 118.958 no . . .
C7 C8 H5 120.898 no . . .
C9 C8 H5 120.060 no . . .
C8 C9 H6 119.740 no . . .
C10 C9 H6 120.042 no . . .
C5 C10 H7 119.285 no . . .
C9 C10 H7 118.901 no . . .
C11 C12 H8 119.077 no . . .
C13 C12 H8 119.671 no . . .
C12 C13 H9 119.377 no . . .
C14 C13 H9 120.282 no . . .
C13 C14 H10 120.015 no . . .
C15 C14 H10 120.600 no . . .
C14 C15 H11 119.694 no . . .
C16 C15 H11 119.567 no . . .
C11 C16 H12 119.073 no . . .
C15 C16 H12 119.887 no . . .
C17 C18 H13 119.582 no . . .
C19 C18 H13 119.652 no . . .
C18 C19 H14 119.956 no . . .
C20 C19 H14 120.124 no . . .
C19 C20 H15 119.684 no . . .
C21 C20 H15 120.261 no . . .
C20 C21 H16 120.263 no . . .
C22 C21 H16 119.766 no . . .
C17 C22 H17 119.057 no . . .
C21 C22 H17 120.238 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 P1 C4 C3 7.14(16) no . . . .
C1 P1 C4 C11 -179.40(19) no . . . .
C4 P1 C1 C2 -7.20(17) no . . . .
C4 P1 C1 C5 -176.6(2) no . . . .
C1 P1 C17 C18 69.19(14) no . . . .
C1 P1 C17 C22 -111.38(13) no . . . .
C17 P1 C1 C2 -112.85(15) no . . . .
C17 P1 C1 C5 77.7(2) no . . . .
C4 P1 C17 C18 -26.51(15) no . . . .
C4 P1 C17 C22 152.93(12) no . . . .
C17 P1 C4 C3 113.64(15) no . . . .
C17 P1 C4 C11 -72.90(19) no . . . .
P1 C1 C2 C3 5.7(3) no . . . .
P1 C1 C5 C6 -11.5(3) no . . . .
P1 C1 C5 C10 166.97(16) no . . . .
C2 C1 C5 C6 -179.0(2) no . . . .
C2 C1 C5 C10 -0.5(4) no . . . .
C5 C1 C2 C3 174.9(2) no . . . .
C1 C2 C3 C4 -0.2(3) no . . . .
C2 C3 C4 P1 -5.4(3) no . . . .
C2 C3 C4 C11 -178.8(2) no . . . .
P1 C4 C11 C12 8.3(4) no . . . .
P1 C4 C11 C16 -171.77(16) no . . . .
C3 C4 C11 C12 -179.4(2) no . . . .
C3 C4 C11 C16 0.5(4) no . . . .
C1 C5 C6 C7 178.8(2) no . . . .
C1 C5 C10 C9 -178.3(2) no . . . .
C6 C5 C10 C9 0.3(4) no . . . .
C10 C5 C6 C7 0.3(4) no . . . .
C5 C6 C7 C8 -0.7(4) no . . . .
C6 C7 C8 C9 0.5(4) no . . . .
C7 C8 C9 C10 0.0(5) no . . . .
C8 C9 C10 C5 -0.4(4) no . . . .
C4 C11 C12 C13 179.3(2) no . . . .
C4 C11 C16 C15 -179.6(2) no . . . .
C12 C11 C16 C15 0.4(4) no . . . .
C16 C11 C12 C13 -0.7(4) no . . . .
C11 C12 C13 C14 0.8(4) no . . . .
C12 C13 C14 C15 -0.7(5) no . . . .
C13 C14 C15 C16 0.4(5) no . . . .
C14 C15 C16 C11 -0.3(5) no . . . .
P1 C17 C18 C19 178.83(12) no . . . .
P1 C17 C22 C21 -179.73(12) no . . . .
C18 C17 C22 C21 -0.3(3) no . . . .
C22 C17 C18 C19 -0.6(3) no . . . .
C17 C18 C19 C20 0.7(3) no . . . .
C18 C19 C20 C21 0.0(3) no . . . .
C19 C20 C21 C22 -0.9(3) no . . . .
C20 C21 C22 C17 1.0(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
P1 C6 3.278(2) no . .
P1 C12 3.258(2) no . .
C1 C18 3.520(4) no . .
C2 C10 2.987(3) no . .
C3 C16 2.988(3) no . .
C4 C18 3.160(4) no . .
C5 C8 2.808(3) no . .
C6 C9 2.743(4) no . .
C7 C10 2.734(3) no . .
C11 C14 2.797(3) no . .
C12 C15 2.742(3) no . .
C12 C17 3.579(2) no . .
C13 C16 2.747(4) no . .
C17 C20 2.776(4) no . .
C18 C21 2.752(3) no . .
C19 C22 2.754(4) no . .
P1 C2 3.579(3) no . 2_556
C2 P1 3.579(3) no . 2_546
P1 H1 3.4847 no . .
P1 H2 3.4879 no . .
P1 H3 2.8746 no . .
P1 H8 2.8392 no . .
P1 H13 2.9171 no . .
P1 H17 2.8460 no . .
C1 H2 3.2191 no . .
C1 H3 2.6603 no . .
C1 H7 2.6452 no . .
C1 H13 3.3842 no . .
C2 H7 2.6873 no . .
C2 H13 3.5397 no . .
C3 H12 2.6812 no . .
C3 H13 3.2226 no . .
C4 H1 3.2084 no . .
C4 H8 2.6499 no . .
C4 H12 2.6403 no . .
C4 H13 2.7403 no . .
C5 H1 2.7397 no . .
C5 H4 3.2500 no . .
C5 H6 3.2617 no . .
C6 H5 3.2303 no . .
C6 H7 3.2131 no . .
C6 H17 3.5855 no . .
C7 H6 3.2063 no . .
C8 H3 3.2188 no . .
C8 H7 3.2186 no . .
C9 H4 3.2019 no . .
C10 H1 2.7518 no . .
C10 H3 3.2138 no . .
C10 H5 3.2266 no . .
C11 H2 2.7473 no . .
C11 H9 3.2476 no . .
C11 H11 3.2480 no . .
C11 H13 3.3142 no . .
C12 H10 3.2293 no . .
C12 H12 3.2182 no . .
C13 H11 3.2053 no . .
C14 H8 3.2245 no . .
C14 H12 3.2241 no . .
C15 H9 3.2091 no . .
C16 H2 2.7528 no . .
C16 H8 3.2197 no . .
C16 H10 3.2289 no . .
C17 H3 3.0857 no . .
C17 H8 2.9992 no . .
C17 H14 3.2409 no . .
C17 H16 3.2384 no . .
C18 H8 3.4867 no . .
C18 H15 3.2253 no . .
C18 H17 3.2158 no . .
C19 H16 3.2220 no . .
C20 H13 3.2238 no . .
C20 H17 3.2287 no . .
C21 H14 3.2217 no . .
C22 H3 2.9967 no . .
C22 H8 3.5934 no . .
C22 H13 3.2190 no . .
C22 H15 3.2299 no . .
H1 H2 2.4159 no . .
H1 H7 2.1879 no . .
H2 H12 2.1817 no . .
H3 H4 2.2948 no . .
H3 H17 2.6843 no . .
H4 H5 2.2993 no . .
H5 H6 2.3009 no . .
H6 H7 2.2951 no . .
H8 H9 2.3033 no . .
H8 H13 3.5931 no . .
H9 H10 2.3030 no . .
H10 H11 2.3062 no . .
H11 H12 2.2978 no . .
H13 H14 2.3086 no . .
H14 H15 2.3022 no . .
H15 H16 2.3144 no . .
H16 H17 2.3143 no . .
P1 H1 3.3052 no . 1_565
P1 H1 3.1499 no . 2_556
P1 H2 3.4303 no . 1_565
C1 H1 3.2334 no . 2_556
C1 H2 3.2614 no . 2_556
C1 H15 3.5979 no . 2_646
C1 H17 3.5342 no . 1_545
C2 H1 3.2261 no . 2_556
C2 H17 3.1949 no . 1_545
C3 H1 3.2562 no . 2_556
C3 H8 3.5632 no . 1_545
C3 H17 3.5543 no . 1_545
C4 H1 3.2778 no . 2_556
C4 H7 3.1491 no . 2_556
C5 H2 2.9673 no . 2_556
C5 H15 2.9389 no . 2_646
C6 H2 3.4219 no . 2_556
C6 H7 3.3883 no . 1_565
C6 H14 3.3466 no . 2_656
C6 H15 3.1876 no . 2_646
C6 H16 3.3518 no . 2_646
C7 H5 3.4356 no . 2_657
C7 H7 3.4603 no . 1_565
C7 H12 3.4032 no . 2_556
C7 H14 3.0850 no . 2_656
C7 H15 3.4842 no . 2_646
C8 H4 3.4552 no . 2_647
C8 H5 3.4018 no . 2_647
C8 H6 3.3105 no . 2_657
C8 H11 3.5746 no . 2_556
C8 H12 3.1190 no . 2_556
C8 H15 3.5613 no . 2_646
C9 H4 3.4071 no . 1_545
C9 H5 3.0938 no . 2_647
C9 H12 3.1331 no . 2_556
C9 H15 3.3243 no . 2_646
C10 H2 3.1438 no . 2_556
C10 H4 3.4762 no . 1_545
C10 H12 3.4389 no . 2_556
C10 H15 2.9963 no . 2_646
C11 H6 3.5260 no . 2_556
C11 H7 3.0866 no . 2_556
C11 H9 3.1845 no . 2_545
C12 H2 3.5758 no . 1_565
C12 H6 3.5253 no . 2_556
C12 H7 3.5463 no . 2_556
C12 H9 3.0733 no . 2_545
C12 H12 3.3465 no . 1_565
C13 H6 3.4270 no . 2_556
C13 H9 3.1232 no . 2_545
C13 H12 3.3466 no . 1_565
C14 H6 3.2972 no . 2_556
C14 H8 3.4082 no . 2_545
C14 H9 3.2834 no . 2_545
C14 H13 3.2795 no . 2_555
C14 H14 3.3969 no . 2_555
C15 H6 3.2697 no . 2_556
C15 H9 3.3833 no . 1_545
C15 H9 3.3688 no . 2_545
C16 H6 3.3780 no . 2_556
C16 H7 3.4780 no . 2_556
C16 H9 3.3745 no . 1_545
C16 H9 3.3212 no . 2_545
C17 H16 3.3234 no . 2_646
C18 H10 3.0837 no . 2_545
C18 H16 3.4606 no . 1_545
C18 H16 3.3607 no . 2_646
C18 H17 3.3700 no . 1_545
C19 H3 3.5974 no . 2_646
C19 H4 3.3270 no . 2_646
C19 H10 3.1674 no . 2_545
C19 H11 3.1539 no . 2_555
C19 H16 3.2497 no . 1_545
C19 H16 3.3665 no . 2_646
C20 H4 3.5913 no . 2_646
C20 H11 3.2189 no . 2_555
C20 H16 3.3119 no . 2_646
C20 H17 3.3910 no . 2_646
C21 H10 3.2701 no . 2_555
C21 H13 3.4370 no . 1_565
C21 H14 3.3810 no . 1_565
C21 H16 3.2494 no . 2_646
C22 H10 3.4382 no . 2_555
C22 H13 3.2133 no . 1_565
C22 H16 3.2612 no . 2_646
H1 P1 3.3052 no . 1_545
H1 P1 3.1499 no . 2_546
H1 C1 3.2334 no . 2_546
H1 C2 3.2261 no . 2_546
H1 C3 3.2562 no . 2_546
H1 C4 3.2778 no . 2_546
H1 H3 3.1653 no . 1_545
H1 H17 3.2478 no . 1_545
H2 P1 3.4303 no . 1_545
H2 C1 3.2614 no . 2_546
H2 C5 2.9673 no . 2_546
H2 C6 3.4219 no . 2_546
H2 C10 3.1438 no . 2_546
H2 C12 3.5758 no . 1_545
H2 H7 3.3720 no . 2_546
H2 H8 2.9795 no . 1_545
H3 C19 3.5974 no . 2_656
H3 H1 3.1653 no . 1_565
H3 H7 3.0832 no . 1_565
H3 H14 3.0649 no . 2_656
H3 H15 3.2548 no . 2_656
H3 H16 3.2091 no . 2_646
H4 C8 3.4552 no . 2_657
H4 C9 3.4071 no . 1_565
H4 C10 3.4762 no . 1_565
H4 C19 3.3270 no . 2_656
H4 C20 3.5913 no . 2_656
H4 H5 2.7004 no . 2_657
H4 H6 3.1138 no . 1_565
H4 H6 3.2633 no . 2_657
H4 H7 3.2278 no . 1_565
H4 H14 2.5743 no . 2_656
H4 H15 3.1040 no . 2_656
H5 C7 3.4356 no . 2_647
H5 C8 3.4018 no . 2_657
H5 C9 3.0938 no . 2_657
H5 H4 2.7004 no . 2_647
H5 H5 3.1657 no . 2_647
H5 H5 3.1657 no . 2_657
H5 H6 2.5793 no . 2_657
H5 H11 3.2577 no . 2_556
H5 H12 3.4392 no . 2_556
H6 C8 3.3105 no . 2_647
H6 C11 3.5260 no . 2_546
H6 C12 3.5253 no . 2_546
H6 C13 3.4270 no . 2_546
H6 C14 3.2972 no . 2_546
H6 C15 3.2697 no . 2_546
H6 C16 3.3780 no . 2_546
H6 H4 3.1138 no . 1_545
H6 H4 3.2633 no . 2_647
H6 H5 2.5793 no . 2_647
H6 H12 3.4599 no . 2_556
H7 C4 3.1491 no . 2_546
H7 C6 3.3883 no . 1_545
H7 C7 3.4603 no . 1_545
H7 C11 3.0866 no . 2_546
H7 C12 3.5463 no . 2_546
H7 C16 3.4780 no . 2_546
H7 H2 3.3720 no . 2_556
H7 H3 3.0832 no . 1_545
H7 H4 3.2278 no . 1_545
H7 H15 3.3615 no . 2_646
H8 C3 3.5632 no . 1_565
H8 C14 3.4082 no . 2_555
H8 H2 2.9795 no . 1_565
H8 H9 3.5139 no . 2_545
H8 H10 3.3708 no . 2_555
H8 H12 3.0557 no . 1_565
H9 C11 3.1845 no . 2_555
H9 C12 3.0733 no . 2_555
H9 C13 3.1232 no . 2_555
H9 C14 3.2834 no . 2_555
H9 C15 3.3833 no . 1_565
H9 C15 3.3688 no . 2_555
H9 C16 3.3745 no . 1_565
H9 C16 3.3212 no . 2_555
H9 H8 3.5139 no . 2_555
H9 H9 3.5511 no . 2_545
H9 H9 3.5511 no . 2_555
H9 H11 3.1188 no . 1_565
H9 H12 3.0895 no . 1_565
H9 H13 3.2499 no . 2_555
H10 C18 3.0837 no . 2_555
H10 C19 3.1674 no . 2_555
H10 C21 3.2701 no . 2_545
H10 C22 3.4382 no . 2_545
H10 H8 3.3708 no . 2_545
H10 H13 2.4787 no . 2_555
H10 H14 2.6655 no . 2_555
H10 H16 3.4406 no . 2_545
H11 C8 3.5746 no . 2_546
H11 C19 3.1539 no . 2_545
H11 C20 3.2189 no . 2_545
H11 H5 3.2577 no . 2_546
H11 H9 3.1188 no . 1_545
H11 H14 3.3277 no . 2_545
H11 H15 3.3784 no . 2_545
H12 C7 3.4032 no . 2_546
H12 C8 3.1190 no . 2_546
H12 C9 3.1331 no . 2_546
H12 C10 3.4389 no . 2_546
H12 C12 3.3465 no . 1_545
H12 C13 3.3466 no . 1_545
H12 H5 3.4392 no . 2_546
H12 H6 3.4599 no . 2_546
H12 H8 3.0557 no . 1_545
H12 H9 3.0895 no . 1_545
H13 C14 3.2795 no . 2_545
H13 C21 3.4370 no . 1_545
H13 C22 3.2133 no . 1_545
H13 H9 3.2499 no . 2_545
H13 H10 2.4787 no . 2_545
H13 H16 3.2238 no . 1_545
H13 H17 2.7621 no . 1_545
H14 C6 3.3466 no . 2_646
H14 C7 3.0850 no . 2_646
H14 C14 3.3969 no . 2_545
H14 C21 3.3810 no . 1_545
H14 H3 3.0649 no . 2_646
H14 H4 2.5743 no . 2_646
H14 H10 2.6655 no . 2_545
H14 H11 3.3277 no . 2_555
H14 H16 2.8077 no . 1_545
H15 C1 3.5979 no . 2_656
H15 C5 2.9389 no . 2_656
H15 C6 3.1876 no . 2_656
H15 C7 3.4842 no . 2_656
H15 C8 3.5613 no . 2_656
H15 C9 3.3243 no . 2_656
H15 C10 2.9963 no . 2_656
H15 H3 3.2548 no . 2_646
H15 H4 3.1040 no . 2_646
H15 H7 3.3615 no . 2_656
H15 H11 3.3784 no . 2_555
H15 H17 3.3050 no . 2_646
H16 C6 3.3518 no . 2_656
H16 C17 3.3234 no . 2_656
H16 C18 3.4606 no . 1_565
H16 C18 3.3607 no . 2_656
H16 C19 3.2497 no . 1_565
H16 C19 3.3665 no . 2_656
H16 C20 3.3119 no . 2_656
H16 C21 3.2494 no . 2_656
H16 C22 3.2612 no . 2_656
H16 H3 3.2091 no . 2_656
H16 H10 3.4406 no . 2_555
H16 H13 3.2238 no . 1_565
H16 H14 2.8077 no . 1_565
H17 C1 3.5342 no . 1_565
H17 C2 3.1949 no . 1_565
H17 C3 3.5543 no . 1_565
H17 C18 3.3700 no . 1_565
H17 C20 3.3910 no . 2_656
H17 H1 3.2478 no . 1_565
H17 H13 2.7621 no . 1_565
H17 H15 3.3050 no . 2_656

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
